module specification

This module relates the physical and chemical behaviour of polyfunctional acyclic and cyclic organic compounds and biomolecules to their structures and electronic properties. Taught classes will be reinforced by practical exercises and spectroscopic problems

CH4002, CH4005

The aims of this module are aligned with the qualification descriptors within the Quality Assurance Agency’sFramework for Higher Education Qualifications.

The module aims to: enable students to relate fundamental organic reactions in terms of generic mechanisms (electrophilic, nucleophilic and neutral) and outcomes (substitution, addition, elimination and rearrangement).   It will allow students to predict physical and chemical properties of organic compounds based on analysis of their electronic and three-dimensional structures, and to rationalise unfamiliar mechanisms thereby. Students will interpret NMR and other spectra of organic molecules, and gain practical experience in selected synthetic techniques.

Acidity/Basicity and the comparison with electrophilic and nucleophilic behaviour. The effect of structure on the acidity of carbonyl compounds; tautomerism and enolate anions, carbocation and carbanion chemistry. carbonyl compounds, their chemical behaviour, keto-enol tautomerism. Compounds studied include conjugated dienes, enamines, allylic and benzylic compounds, aromatic and heteroaromatic ring systems, unsaturated carbonyl compounds, diols and hydroxy-carbonyl compounds.
Mechanistic comparisons of the SN1, SN2, E1 and E2 reactions, factors influencing one pathway over another. Mechanistic evaluation of addition and rearrangement reactions, free radical reactions and simple pericyclic reactions. Polyfunctional aliphatic compounds - physical and chemical properties.
Alicyclic chemistry - effect of ring size on the stability of alicyclic compounds; types and causes of strain. Methods for the synthesis of alicyclic compounds with rings of 3-20 carbon atoms: intramolecular carbanion condensation reactions, the acyloin and related reactions. Conformation in alicyclic compounds and carbohydrates: effects of conformation on rate and outcome of reactions in cyclohexane derivatives; differences between reactions of alicyclic compounds and their acyclic counterparts.
The chemistry of aromatic ring systems; electrophilic and nucleophilic substitution reactions. Heterocyclic aromatic systems 5- and 6-membered rings.
Simple MO theory: thermal and excited state reactions of conjugated π-systems. Ethene, butadiene, hexatriene: electrocyclic reactions, the Diels-Alder and higher order cycloadditions,
Spectroscopic characterisation of organic compounds: use of NMR in structure elucidation of complex systems: 1H decoupled spectra, 1H-1H and 1H-13C correlation spectra.

Acquisition of knowledge of the subject matter of this module will be promoted through lecturer-led lectures (48 hours) and tutorial workshops (24 hours); directed web-based learning and through the guided use of student-centred learning resources. Practical classes (15 hours) and tutorials will be used to consolidate the student with guidance for directed activities. Self managed time and private study (213h) should be spread out over the whole year and not left until the final weeks.

1. Classify different organic reactions in terms of their mechanisms and outcomes;
2. Interpret and predict the physical and chemical behaviour of aliphatic compounds containing more than one functional group [A3];
3. Apply simple LCAO and MO theory to predicting the outcome of reactions involving molecules containing conjugated π-systems [A3];
4. Recognise the conformational limitations placed on cyclic structures and thus explain differences in their chemical behaviour with those of their aliphatic counterparts [A2];
5. Perform selected synthetic and purification techniques, and relate to the lecture material
6. Interpret 1H, 13C, and 1H-13C correlation NMR spectra in elucidation of structures of polyfunctional organic compounds [A3].

This module will be assessed by: a time-constrained progress test (1 hour), an end of year examination (2 hours), a 10-minute powerpoint presentation (on a named organic chemistry reaction) and a portfolio of practical results. The progress test, 10-minute presentation and practical portfolio will provide both formative and summative assessment, the examination summative assessment alone.

The Progress Test (20%) will assess the students’ knowledge of all organic reaction mechanisms covered in the first semester.

A practical portfolio (30%) will be submitted to assess the students’ ability to acquire, manipulate and interpret experimental data, and to report the findings in an appropriate scientific manner.

A 10-minute powerpoint presentation (15%) will assess the students’ ability to independently research an organic chemistry reaction of their choice, which was not covered in the lectures. They will need to demonstrate clearly that they have understood the detailed mechanisms involved, and give examples of where the reaction has been applied, e.g., to the synthesis of a modern pharmaceutical, or a complex natural product.

An end-of-module examination (35%) will assess the students’ knowledge of organic reaction mechanisms, practical procedures and spectroscopic characterisation. Students will be required to draw on relevant material delivered throughout the course to predict and explain specific outcomes of hitherto unseen reactions.

To pass the module students must achieve a minimum aggregate mark of 40%. There will be an attendance requirement for the practical sessions. If the module is passed on reassessment, then the maximum mark awarded will be 40%.

Cox BG, (2013) Acids and Bases: Solvent Effects on Acid-Base Strength Oxford UP
McMurry JE. (2008) Organic Chemistry 8th Edn. Brooks/Cole: Cengage learning
Vollhardt P, Schore N (2011) Organic Chemistry: Structure and Function 6th Edn. Freeman
Grossel M (1997) Alicyclic Chemistry. Oxford Chemistry Primers 54, OUP
Hornby M, Peach J (2001). Foundations of Organic Chemistry: worked examples. Oxford Chemistry Primers 87, OUP
Maskill H (1996) Mechanisms of Organic Reactions. Oxford Chemistry Primers 45, OUP
Scudder PH, (1992) Electron Flow in Organic Chemistry John Wiley & Sons Inc.